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Segesterone acetate

Segesterone acetate
Clinical data
Trade namesNestorone, Elcometrine, Annovera
Other namesSGA; SA; Nestorone; Nestoron; Elcometrine; ST-1435; AC-6844; CS-0411; 16-Methylene-17α-acetoxy-19-norprogesterone; 16-Methylene-17α-acetoxy-19-norpregn-4-ene-3,20-dione
Routes of
administration		Subcutaneous implant, vaginal ring, transdermal patch[1]
Drug classProgestogen; Progestin; Progestogen ester
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityOral: 10%[1][2]
Protein binding95% (to albumin and not to SHBGTooltip sex hormone-binding globulin[1][3][4]
MetabolismHydroxylation (CYP3A4), reduction (5α-reductase)
Elimination half-lifeVaginal ring: 4.5 hours[4]
Parenteral: 24–72 hours[5][6]
Oral: 1–2 hours[1]
Identifiers
  • [(8R,9S,10R,13S,14S,17R)-17-acetyl-13-methyl-16-methylidene-3-oxo-2,6,7,8,9,10,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H30O4
Molar mass370.489 g·mol−1
3D model (JSmol)
  • O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@](OC(=O)C)(C(=C)\C[C@H]3[C@@H]1CC2)C(=O)C)C)CC4
  • InChI=1S/C23H30O4/c1-13-11-21-20-7-5-16-12-17(26)6-8-18(16)19(20)9-10-22(21,4)23(13,14(2)24)27-15(3)25/h12,18-21H,1,5-11H2,2-4H3/t18-,19+,20+,21-,22-,23-/m0/s1
  • Key:CKFBRGLGTWAVLG-GOMYTPFNSA-N

Segesterone acetate (SGA), sold under the brand names Nestorone, Elcometrine, and Annovera, is a progestin medication which is used in birth control and in the treatment of endometriosis in the United States, Brazil, and other South American countries.[1][4][7] It is available both alone and in combination with an estrogen.[1][4][7] It is not effective by mouth and must be given by other routes, most typically as a vaginal ring or implant that is placed into fat.[1][4][8]

Side effects of SGA are similar to those of other progestins. SGA is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[1][3][9][10] It has some affinity for the glucocorticoid receptor and has no other important hormonal activity.[1][3][9][10]

SGA was developed by the Population Council and was introduced for medical use by 2000.[7][11] It is under development in the United States and Europe as a gel in combination with estradiol or testosterone for use as a method of birth control in women and in men, respectively.[12][13][14][15] On August 10, 2018, a first-of-its-kind one-year contraceptive vaginal ring containing segesterone acetate in combination with ethinyl estradiol was approved in the United States.[4][16] It is marketed under the brand name Annovera and is reusable for up to one year as a method of birth control in women. Annovera does not require refrigeration which is very useful for low resource areas.[4][17]

  1. ^ a b c d e f g h i Lemke TL, Williams DA, Roche VT, Zito SW (24 January 2012). "Chapter 41: Women's Health". Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 1403. ISBN 978-1-60913-345-0. Retrieved 13 September 2012.
  2. ^ Sitruk-Ware R (15 May 2001). "Progestins and the cardiovascular system". In Genazzani AR (ed.). Hormone Replacement Therapy and Cardiovascular Disease: The Current Status of Research and Practice. CRC Press. pp. 95–. ISBN 978-1-84214-038-3.
  3. ^ a b c Cite error: The named reference pmid16112947 was invoked but never defined (see the help page).
  4. ^ a b c d e f g "ANNOVERATM (segesterone acetate and ethinyl estradiol vaginal system)" (PDF). Population Council. U.S. Food and Drug Administration. 2018.
  5. ^ Rabe T, Goeckenjan M, Ahrendt HJ, Crosignani PG, Dinger JC, Mueck AO, et al. (October 2011). "Oral Contraceptive Pills: Combinations, Dosages and the Rationale behind 50 Years or Oral Hormonal Contraceptive Development" (PDF). Journal für Reproduktionsmedizin und Endokrinologie-Journal of Reproductive Medicine and Endocrinology. 8 (1): 58–129.
  6. ^ Fraser IS, Weisberg E, Kumar N, Kumar S, Humberstone AJ, McCrossin L, et al. (December 2007). "An initial pharmacokinetic study with a Metered Dose Transdermal Systemfor delivery of the progestogen Nestorone as a possible future contraceptive". Contraception. 76 (6): 432–438. doi:10.1016/j.contraception.2007.08.006. PMID 18061700.
  7. ^ a b c Cite error: The named reference Croxatto2000 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference RajagopalanMukherjee2004 was invoked but never defined (see the help page).
  9. ^ a b Cite error: The named reference pmid21828184 was invoked but never defined (see the help page).
  10. ^ a b Cite error: The named reference pmid11108869 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference PrasadShrivastav2015 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference AdisInsight was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference pmid22791756 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference PopCouncil-1 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference PopCouncil-2 was invoked but never defined (see the help page).
  16. ^ "FDA approves new vaginal ring for one year of birth control". Food and Drug Administration. 24 March 2020.
  17. ^ Cite error: The named reference PopCouncil-3 was invoked but never defined (see the help page).

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